Herbicidal (oxaalkyl) phenyl-substituted heterocycles

ABSTRACT

It has now been found that certain novel (oxaalkyl)phenyl-substituted heterocycles are useful as pre-emergent and post-emergent herbicides. These compounds are represented by formula I: ##STR1## where Q is a heterocycle and X, Y, R, R 1 , R 2 , and R 3  are substituents as described in the specification. Preferred are those compounds where Y and R are chloro; R 1  and R 2  are hydrogen or methyl; R 3  is hydrogen or alkylaminocarbonyl; X is fluorine; and Q is a 1-substituted-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl.

This application claims benefit to provisional application Ser. No.60/052,368 filed Jul. 11, 1997.

BACKGROUND OF THE INVENTION

This invention relates generally to novel herbicidal compounds andmethods for their use in controlling unwanted plant species inagriculture. In particular, it pertains to herbicidal(oxaalkyl)phenyl-substituted heterocycles, and more particularly itpertains to herbicidal (oxaalkyl)phenyl-substituted heterocycles wherethe oxaalkyl moiety of the (oxaalkyl)phenyl is substituted and theheterocycle is a1-substituted-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl, a4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yl, a4-halo-5-difluoromethoxy-1-methylpyrazol-3-yl, a3,4,5,6-tetrahydrophthalimid-1-yl, a1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazole-5-on-1-yl, a3-chloro-4,5,6,7-tetrahydroindazol-2-yl, a5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-A]pyridin-3(2H)-on-2-yl,5,6,7,8-tetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazineimin-1-yl ora 4-methyl-1,2,4-triazine-3,5-dion-2-yl moiety.

There is a continuing demand for new herbicides. Herbicides are usefulfor controlling unwanted vegetation which may otherwise causesignificant damage to crops such as wheat, corn, soybeans and cotton, toname a few. For crop protection, so-called "selective" herbicides aredesired which can control the weeds without damaging the crop. Suchcrops are said to exhibit tolerance to the herbicide. In certain othersituations, it is desirable to use herbicides that provide completevegetation control such as in areas around railroad tracks and otherstructures. While many commercial products are available that provideselective or complete vegetation control, the demand exists for new,safe herbicides that are more effective and less costly.

German Offenlegungsschrift DE 4237920A1 (Ciba-Geigy AG) describesherbicidally active compounds of the following formula: ##STR2## amongwhich are compounds where W is N(R¹)C═O; R¹ is C₁ -C₄ -alkyl, C₁ -C₄-haloalkyl, C₁ -C₄ -alkenyl, or C₁ -C₄ -alkynyl; R² is halogen or cyano;R³ is hydrogen or halogen; R⁴ is hydrogen or C₁ -C₄ -alkyl; R⁵ is C₁ -C₄-alkyl or C₁ -C₄ -haloalkyl; and Q is CR⁶ R⁷ R⁸ where R⁶ and R⁷ arehydrogen or alkyl; and R⁸ is X₁ R⁹ where X₁ is oxygen; R⁹ is hydrogen orC(═X₂)R¹⁰ where X₂ is oxygen; and R¹⁰ is C₁ -C₅ -alkyl or C₁ -C₄-alkoxy.

British Patent GB 2,289,893 (BASF Akt.) describes herbicidally activecompounds of the following formula: ##STR3## among which are compoundswhere R¹ is halogen or cyano; R² is hydrogen or halogen; R³, R⁴ arehydrogen, halogen, or alkyl; R⁵, R⁶ are hydrogen or alkyl; and R⁷ ishydrogen, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, orcycloalkylaminocarbonyl.

SUMMARY OF THE INVENTION

It has now been found that certain novel (oxaalkyl)phenyl-substitutedheterocycles are useful as pre-emergent and post-emergent herbicides.These compounds are represented by formula I: ##STR4## where Q is aheterocycle, and X, Y, R, R¹, R², and R³ are substituents as describedbelow. Preferred compounds include those where Y and R are chloro; R¹and R² are hydrogen or methyl; R³ is hydrogen or alkylaminocarbonyl; Xis fluorine; and Q is a1-substituted-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl.

DETAILED DESCRIPTION OF THE INVENTION

Certain novel (oxaalkyl)phenyl-substituted heterocycles are useful aspre-emergent and post-emergent herbicides. These compounds arerepresented by formula I: ##STR5## R is hydrogen, halogen, or alkyl; R¹is hydrogen, cyano, or alkyl;

R² is hydrogen, or alkyl;

R³ is hydrogen, straight or branched chain alkyl carbonyl,alkoxycarbonyl, alkylaminocarbonyl, or cycloalkylaminocarbonyl;

X is hydrogen or halogen;

Y is halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, or nitro;

R⁴ is hydrogen, amino, straight or branched chain alkyl, haloalkyl,cyanoalkyl, alkoxyalkyl, arylalkyl, alkoxycarbonylalkyl, arylalkyl,alkoxycarbonylalkyl, alkenyl, alkynyl, or a salt-forming ion; and

R⁵ is halogen.

For Q in formula I, the above structural moieties may also be identifiedby their chemical name as follows: ##STR6## where "A" is1-substituted-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl, "B" is4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yl, "C"is 4-halo-5-difluoromethoxy-1-methylpyrazol-3-yl, "D" is3,4,5,6-tetrahydrophthalimid-1-yl, "E" is1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazole-5-on-1-yl, "F" is3-chloro-4,5,6,7-tetrahydroindazol-2-yl, "G" is5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-A]pyridin-3(2H)-on-2-yl, "H" is5,6,7,8-tetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazineimin-1-yl,and "J" is 4-methyl-1,2,4-triazine-3,5-dion-2-yl.

One aspect of this invention relates to compounds of formula I where Qis 1-substituted-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl and R,R¹, R², R³, X, Y, and R⁴ are as described above.

Another aspect of this invention relates to compounds of formula I whereQ is 4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yland R, R¹, R², R³, X, and Y are as described above.

Another aspect of this invention relates to compounds of formula I whereQ is 4-halo-5-difluoromethoxy-1-methylpyrazol-3-yl and R, R¹, R², R³, X,Y, and R⁵ are as described above.

Another aspect of this invention relates to compounds of formula I whereQ is 3,4,5,6-tetrahydrophthalimid-1-yl and R, R¹, R², R³, X, and Y areas described above.

Another aspect of this invention relates to compounds of formula I whereQ is 1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazole-5-on-1-yl and R, R¹,R², R³, X, and Y are as described above.

Another aspect of this invention relates to compounds of formula I whereQ is 3-chloro-4,5,6,7-tetrahydroindazol-2-yl and R, R¹, R², R³, X, and Yare as described above.

Another aspect of this invention relates to compounds of formula I whereQ is 5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-A]pyridin-3(2H)-on-2-yl andR, R¹, R², R³, X, and Y are as described above.

Another aspect of this invention relates to compounds of formula I whereQ is5,6,7,8-tetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazineimin-1-yland R, R¹, R², R³, X, and Y are as described above.

Another aspect of this invention relates to compounds of formula I whereQ is 4-methyl-1,2,4-triazine-3,5-dion-2-yl and R, R¹, R², R³, X, and Yare as described above.

Preferred are those of formula I where Y and R are chloro; R¹ and R² arehydrogen or methyl; R³ is hydrogen or alkylaminocarbonyl; and X isfluoro.

Particularly preferred are those compounds of formula I where Q is1-substituted-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl; Y and Rare chloro; R¹ and R² are hydrogen or methyl; R³ is hydrogen ormethylaminocarbonyl; X is fluoro; and R⁴ is methyl or amino.

As used in this specification and unless otherwise indicated the terms"alkyl", "alkenyl", "alkynyl", used alone or as part of a larger moietyincludes 1 to 6 carbon atoms, and the term "cycloalkyl" includes 3 to 8carbon atoms. "Halogen" refers to fluorine, bromine, or chlorine."Salt-forming ion" refers to sodium, potassium, lithium, barium orcalcium.

The (oxaalkyl)phenyl-substituted heterocycles of formula I may beprepared by the methods described below or by methods similar to thoseknown to one skilled in the art for similar compounds. ##STR7##

Scheme 1 above illustrates a general procedure for preparing compoundsof formula I where R is chloro, and R¹ and R² are hydrogen or alkyl. Thestarting aniline 1 may be prepared according to known methods, such asthose taught in U.S. Pat. Nos. 5,041,155, 4,954,159, or 4,932,996.Diazotization of 1 and reaction with an appropriate alkenyl alcohol asshown in step (a) affords the alcohol 2. Alcohol 2 may be acylated withan appropriate anhydride according to step (b) to provide 2a orconverted with an isocyanate according to step (c) to provide carbamate2b.

Procedures for some of the methods that are useful to prepare compoundsof this invention are given in the Examples below.

EXAMPLE 12-CHLORO-3-METHYL-1-[2-CHLORO-4-FLUORO-5-[1-METHYL-6-TRIFLUOROMETHYL-2,4(1H,3H)-PYRIMIDINDION-3-YL]PHENYL]BUTAN-3-OL(Compound 1)

A mixture of 2.0 grams (0.015 mole) of copper(II) chloride, and 1.5grams (0.015 mole) of tert.-butyl nitrite in 10.2 mL (0.10 mole) of2-methyl-3-buten-2-ol was rapidly stirred, and a solution of 2.9 grams(0.010 mole) of1-methyl-6-trifluoromethyl-3-(5-amino-4-chloro-2-fluorophenyl)-2,4(1H,3H)pyrimidinedionein 80 mL of acetonitrile was added slowly. Upon completion of addition,the reaction mixture was stirred for about one hour, then it was pouredinto water. The mixture was extracted with diethyl ether, and theextract was dried with magnesium sulfate. The extract was filtered, andthe filtrate was concentrated under reduced pressure to a residue. Theresidue was purified by column chormatography on silica gel using ethylacetate in methylene chloride, yielding 3.8 grams of Compound 1. The NMRspectrum was consistent with the proposed structure.

EXAMPLE 22-CHLORO-3-METHYL-1-[2-CHLORO-4-FLUORO-5-[1-METHYL-6-TRIFLUOROMETHYL-2,4(1H,3H)-PYRIMIDINDION-3-YL]PHENYL]BUTAN-3-YLACETATE (Compound 16)

A mixture of 0.95 gram (0.0021 mole) of2-chloro-3-methyl-1-[2chloro-4-fluoro-5-[1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidindion-3-yl]phenyl]butan-3-ol,0.26 gram (0.0026 mole) of acetic anhydride, and 0.39 gram (0.0032 mole)of 4-dimethylaminopyridine in 5 mL of methylene chloride was stirred atambient temperature for about 18 hours. The reaction mixture was thendiluted with water and extracted with three 45 mL portions of ethylacetate. The combined extracts were dried with magnesium sulfate andfiltered. The filtrate was concentrated under reduced pressure to aresidue. The residue was purified by column chormatography on silica gelusing ethyl acetate in heptane, yielding 0.66 gram of Compound 16, mp40-50° C. The NMR spectrum was consistent with the proposed structure.

EXAMPLE 32-CHLORO-1-[2-CHLORO-4-FLUORO-5-[4DIFLUOROMETHYL-4,5-DIHYDRO-3-METHYL-1,2,4-TRIAZOL-5(1H)-ON-1-YL]PHENYL]PROPAN-3-YLMETHYLCARBAMATE (Compound 31)

A solution of 0.50 gram (0.0013 mole) of2-chloro-1-[2-chloro-fluoro-5-[4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yl]phenyl]propan-3-ol(prepared in the manner of Example 1), 0.23 gram (0.0040 mole) of methylisocyanate, and two drops of dibutyltin diacetate in about 20 mL ofmethylene chloride was stirred at ambient temperature for 18 hours. Thecrude product was purified by column chormatography on silica gel usingethyl acetate in methylene chloride, yielding 0.43 gram of Compound 31.The NMR spectrum was consistent with the proposed structure.

Table 1 below shows representative compounds of the present invention.

                                      TABLE 1                                     __________________________________________________________________________    Herbicidal (oxaalkyl)phenyl-substituted heterocycles                           ##STR8##                                                                     where Q is one of the following moieties:                                      ##STR9##                                                                                  ##STR10##                                                                                  ##STR11##                                                                                  ##STR12##                               ##STR13##                                                                                 ##STR14##                                                                                  ##STR15##                                                                                  ##STR16##                               ##STR17##                                                                    Cmpd                                                                          No.      R   R.sup.1                                                                            R.sup.2                                                                              R.sup.3                                                                               X                                                                                Y    Q   R.sup.4 or                       __________________________________________________________________________                                               R.sup.5                             1          CH.sub.3                                                                           CH.sub.3                                                                               H          Cl                                                                               A      CH.sub.3                        2        Cl                                                                              CH.sub.3                                                                          CH.sub.3                                                                               H        F                                                                               Cl  B    --                                3        Cl                                                                              CH.sub.3                                                                          CH.sub.3                                                                               H        F                                                                               Cl  C       Cl                             4        H                                                                                CH.sub.3                                                                         CH.sub.3                                                                               H        H                                                                               Cl  A      CH.sub.3                        5        Cl                                                                              CH.sub.3                                                                          CH.sub.3                                                                               H        H                                                                               Cl  A      CH.sub.3                        6        Br                                                                               CH.sub.3                                                                          CH.sub.3                                                                              H         Cl    A      CH.sub.3                       7        Br                                                                               CH.sub.3                                                                          CH.sub.3                                                                              H         Cl    A      CH.sub.3                       8        Cl                                                                               CH.sub.3                                                                          CH.sub.3                                                                              H         Br    A      CH.sub.3                       9        Cl                                                                               CH.sub.3                                                                          CH.sub.3                                                                              H         C.tbd.N                                                                           A       CH.sub.3                       10       H    CH.sub.3                                                                         CH.sub.3                                                                              H         Cl    A      CH.sub.3                      11      CH.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                              H         Cl    A      CH.sub.3                      12       Cl                                                                                C.sub.2 H.sub.5                                                                  CH.sub.3                                                                             H      F    Cl    A     CH.sub.3                       13       Cl                                                                                C.tbd.N                                                                         --CH.sub.3                                                                             H          Cl    A     CH.sub.3                       14       Cl                                                                                CH.sub.3                                                                          CH.sub.3                                                                              H         C.tbd.N                                                                           A       NH.sub.2                       15       Cl                                                                                CH.sub.3                                                                          CH.sub.3                                                                              H         C.tbd.N                                                                           B       --                             16       Cl                                                                                CH.sub.3                                                                          CH.sub.3                                                                            COCH.sub.3                                                                              F                                                                               Cl    A     CH.sub.3                       17       Cl                                                                                CH.sub.3                                                                          CH.sub.3                                                                            COCH.sub.3                                                                              F                                                                               Cl    B     --                             18       Cl                                                                                CH.sub.3                                                                          CH.sub.3                                                                            COCH.sub.3                                                                              F                                                                               Cl    C      Cl                            19       Cl                                                                                 H                                                                                 CH.sub.3                                                                             H         Cl    A     CH.sub.3                       20       Cl                                                                                 H                                                                                  H                                                                                    H        Cl    A     CH.sub.3                       21       Cl                                                                                 H                                                                                  H                                                                                  COCH.sub.3                                                                             F                                                                               Cl    A     CH.sub.3                       22       Cl                                                                                 H                                                                                  H                                                                                    H        Cl    A     NH.sub.2                       23       Cl                                                                                 H                                                                                  H                                                                                  COCH.sub.3                                                                             F                                                                               Cl    A     NH.sub.2                       24       Cl                                                                                 H                                                                                  H                                                                                    H        Cl    B --                                 25       Cl                                                                              CH.sub.3                                                                          CH.sub.3                                                                                H         Cl    D     --                             26       Cl                                                                                CH.sub.3                                                                          CH.sub.3                                                                              H         Cl    C      Br                            27       Cl                                                                                CH.sub.3                                                                          CH.sub.3                                                                            COCH.sub.3                                                                              F                                                                               Cl    C      Br                            28       Cl                                                                                 H                                                                                  H                                                                                 CONHCH.sub.3                                                                           F  Cl    A     CH.sub.3                       29       Cl                                                                                 H                                                                                 H    CONHCH(CH.sub.3).sub.2                                                                F   Cl    A     CH.sub.3                       30       Cl                                                                                 H                                                                                  H                                                                                  CO.sub.2 CH.sub.3                                                                     F  Cl    A     CH.sub.3                       31       Cl                                                                                 H                                                                                  H                                                                                 CONHCH.sub.3                                                                           F  Cl    B    --                              32       Cl                                                                                 H                                                                                  H                                                                                 CONHC.sub.2 H.sub.5                                                                   F   Cl    B  --                                33       Cl                                                                                 H                                                                                  H                                                                                 CONHC(CH.sub.3).sub.3                                                                 F   Cl    B    --                              34       Cl                                                                                 H                                                                                  H                                                                                 CONHCH(CH.sub.3).sub.2                                                                F   Cl    B    --                              35       Cl                                                                                 H                                                                                  H                                                                                 CONH-cyclohexyl                                                                         F                                                                               Cl    B    --                              36       Cl                                                                                 H                                                                                  H                                                                                 CONH(CH.sub.2).sub.5 CH.sub.3                                                        F    Cl    B   --                               37       Cl                                                                                CH.sub.3                                                                          CH.sub.3                                                                              H        Cll    B    --                              38       Cl                                                                                CH.sub.3                                                                          CH.sub.3                                                                              H         Cl    E    --                              39       Cl                                                                                CH.sub.3                                                                          CH.sub.3                                                                           CONHCH.sub.3                                                                            F  Cl    E   --                               40       Cl                                                                                 H                                                                                  H                                                                                    H        Cl    E    --                              41       Cl                                                                                CH.sub.3                                                                          CH.sub.3                                                                            COCH.sub.3                                                                              F                                                                               Cl    E   --                               42       Cl                                                                                CH.sub.3                                                                          CH.sub.3                                                                              H         Cl    F    --                              43       Cl                                                                                 H                                                                                  H                                                                                  COCH.sub.3                                                                             F                                                                               Cl    F   --                               44       Cl                                                                                 H                                                                                  H                                                                                    H       Cll    F    --                              45       Cl                                                                                 H                                                                                  H                                                                                    H        Cl    G    --                              46       Cl                                                                                CH.sub.3                                                                          CH.sub.3                                                                            COCH.sub.3                                                                              F                                                                               Cl    G    --                              47      Cl    H                                                                                  H                                                                                    H        Cl    H    --                              48       H     H                                                                                 H                                                                                    H        Cl    J    --                              49       Cl                                                                                CH.sub.3                                                                          CH.sub.3                                                                              H         Cl    J    --                              50      CH.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                              H        Cll    J    --                              51       Cl                                                                                CH.sub.3                                                                          CH.sub.3                                                                              H         Cl    A      H                             52        Cl                                                                               CH.sub.3                                                                          CH.sub.3                                                                             H          Cl   A       C.sub.2 H.sub.5               53        Cl                                                                               CH.sub.3                                                                          CH.sub.3                                                                             H          Cl   A      n-C.sub.3 H.sub.7              54        Cl                                                                               CH.sub.3                                                                          CH.sub.3                                                                             H          Cl   A      CH(CH.sub.3).sub.2             55        Cl                                                                               CH.sub.3                                                                          CH.sub.3                                                                             H          Cl   A      CH.sub.2 CN                    56        Cl                                                                               CH.sub.3                                                                          CH.sub.3                                                                             H          Cl   A      CH.sub.2 C.sub.6 H.sub.5       57        Cl                                                                               CH.sub.3                                                                          CH.sub.3                                                                             H          Cl   A      CH.sub.2 C.tbd.CH              58        Cl                                                                               CH.sub.3                                                                          CH.sub.3                                                                             H          Cl   A      CH.sub.2 OCH.sub.3             59        Cl                                                                               CH.sub.3                                                                          CH.sub.3                                                                             H          Cl   A    CH.sub.2 CO.sub.2 C.sub.2                                                   H.sub.5                            60        Cl                                                                               CH.sub.3                                                                          CH.sub.3                                                                             H          Cl   A    CH.sub.2 CH═CH.sub.2         61        Cl                                                                               CH.sub.3                                                                          CH.sub.3                                                                             H          Cl   A       NH.sub.2                      62        Cl                                                                               CH.sub.3                                                                          CH.sub.3                                                                             H          Cl   A      CHF.sub.2                      63        Cl                                                                               CH.sub.3                                                                          CH.sub.3                                                                             H          Cl   A       Na                            64        Cl                                                                               CH.sub.3                                                                          CH.sub.3                                                                             H          Cl   A    CH.sub.2 CH.sub.2 CH.sub.2                                                  F                                  65        Cl                                                                               CH.sub.3                                                                          CH.sub.3                                                                             H          CH.sub.3                                                                          A        CH.sub.3                      66        Cl                                                                               CH.sub.3                                                                          CH.sub.3                                                                             H          CF.sub.3                                                                          A        CH.sub.3                      67        Cl                                                                               CH.sub.3                                                                          CH.sub.3                                                                             H          OCH A        CH.sub.3                                                           F.sub.2                                  68        Cl                                                                               CH.sub.3                                                                          CH.sub.3                                                                             H          NO.sub.2                                                                          A        CH.sub.3                      69        Cl                                                                               CH.sub.3                                                                          CH.sub.3                                                                             H          OCH.sub.3                                                                         A        CH.sub.3                      __________________________________________________________________________

                  TABLE 2                                                         ______________________________________                                        Characterizing Data                                                                       Melting Point °C.                                                                          Melting Point °C.                      Cmpd No      Physical State                                                                               Cmpd No                                                                                Physical State                           ______________________________________                                         1      132-135       31       136-137                                        2                                         119-120                             3                                          OIL                                16                40-50 SOFTENS                                                                           34            101-102                             17                    OIL                                                                                               125-126                             18                    OIL                                                                                                71-73                              24                    OIL                                                                                                OIL                                ______________________________________                                    

Biological Testing

The (oxaalkyl)phenyl-substituted heterocycles of this invention weretested for pre- and postemergence herbicidal activity using a variety ofcrops and weeds. The test plants included soybean (Glycine max var.Winchester), field corn (Zea mays var. Pioneer 3732), wheat (Triticumaestivum var. Lew), morningglory (Ipomea lacunosa or Ipomea hederacea),leaf (Abutilon theophrasti), green foxtail (Setaria viridis),Johnsongrass (Sorghum halepense), blackgrass (Aloepecurus myosuroides),common chickweed (Stellaria media), and common cocklebur (Xanthiumstrumarium L.).

For preemergence testing, two disposable fiber flats (8 cm×15 cm×25 cm)for each rate of application of each candidate herbicide were filled toan approximate depth of 6.5 cm with steam-sterilized sandy loam soil.The soil was leveled and impressed with a template to provide fiveevenly spaced furrows 13 cm long and 0.5 cm deep in each flat. Seeds ofsoybean, wheat, corn, green foxtail, and johnsongrass were planted inthe furrows of the first flat, and seeds of velvetleaf, morningglory,common chickweed, cocklebur, and blackgrass were planted in the furrowsof the second flat. The five-row template was employed to firmly pressthe seeds into place. A topping soil of equal portions of sand and sandyloam soil was placed uniformly on top of each flat to a depth ofapproximately 0.5 cm. Flats for postemergence testing were prepared inthe same manner except that they were planted 9-14 days prior to thepreemergence flats and were placed in a greenhouse and watered, thusallowing the seeds to germinate and the foliage to develop.

In both pre- and postemergence tests, a stock solution of the candidateherbicide was prepared by dissolving 0.27 g of the compound in 20 mL ofwater/acetone (50/50) containing 0.5% v/v sorbitan monolaurate. For anapplication rate of 3000 g/ha of herbicide a 10 mL portion of the stocksolution was diluted with water/acetone (50/50) to 45 mL. The volumes ofstock solution and diluent used to prepare solutions for lowerapplication rates are shown in the following table:

    ______________________________________                                         Application                                                                           Volume of  Volume of   Total Volume                                  Rate            Stock Solution                                                                        Acetone/Water                                                                             of Spray Solution                         (g/ha)             (mL)                                                                                                     (mL)                            ______________________________________                                        3000       10            35      45                                           1000                                           45                             300                                            45                             100                                            45.3                           30                                             45.1                           10                                             45.03                          3                                              45.01                          ______________________________________                                    

The preemergence flats were initially subjected to a light water spray.The four flats were placed two by two along a conveyor belt (i.e., thetwo preemergence followed by the two postemergence flats). The conveyorbelt fed under a spray nozzle mounted about ten inches above thepostemergent foliage. The preemergent flats were elevated on the belt sothat the soil surface was at the same level below the spray nozzle asthe foliage canopy of the postemergent plants. The spray of herbicidalsolution was commenced and once stabilized, the flats were passed underthe spray at a speed to receive a coverage equivalent of 1000 L/ha. Atthis coverage the application rates are those shown in the above tablefor the individual herbicidal solutions. The preemergence flats werewatered immediately thereafter, placed in the greenhouse and wateredregularly at the soil surface. The postemergence flats were immediatelyplaced in the green-house and not watered until 24 hours after treatmentwith the test solution. Thereafter they were regularly watered at groundlevel. After 12-17 days the plants were examined and the phytotoxicitydata were recorded.

Herbicidal activity data at selected application rates are given forvarious components of this invention in Table 3 and Table 4. The testcompounds are identified by numbers which correspond to those in Table1.

Phytotoxicity data were taken as percent control. Percent control was bya method similar to the 0 to 1 00 rating system disclosed in "ResearchMethods in Weed Science," 2nd ed., B. Truelove, Ed.; Southern WeedScience Society; Auburn University, Auburn, Ala., 1977. The ratingsystem is as follows:

    ______________________________________                                        Herbicide Rating System                                                         Rating   Description                                                        Percent                         Crop                                                                                                Weed                    Control                      Description                                                                                     Description                    ______________________________________                                          0       No effect      No crop No weed                                                                                     control                                                             or injury                                10                                           Very poor                                                                      weed                                                                         control                          20                                             Poor weed                                                                   control                                                                   stunting or                                                                   stand loss                           30                                            Poor to                                                                   deficientunced                                                                weed not lasting                                                             control                              40                  Moderate                                                                                          Deficientinjury,                                                                  weedually                                                                         control                       50                                           Deficient to                                                                moderateng,                                                                weedery doubtful                                                                           control                  60                       Lasting crop                                                                                     Moderate                                                    injury, no                                                                                        weed                                                       recovery                                                                                           control                       70                          Heavy injury and                                                                          Control                                                            stand loss                                                                                     somewhat                                                         less than                                                                     satisfactory                                 80                                      Satisfactoryrly des-                                                             to goodoyed, a few                                                                weedvivors                                                                                      control      90                             Only occasional                                                                         Very good                                                           live plants left                                                                       to excel-                                                                                               lent                                         control                                      100                              Complete crop                                                                           Complete                                                                        destruction                      ______________________________________                                    

The compounds of the present invention were tested in the laboratory aswater/acetone (50/50) solutions containing 0.5% v/v sorbitan monolaurateemulsifier. It is expected that all formulations normally employed inapplications of herbicides would be usable with the compounds of thepresent invention. These include wettable powders, emulsifiableconcentrates, water suspensions, flowable concentrates, and the like.The pre- and post-emergence activity of selected compounds is shown inTables 3 and 4.

                                      TABLE 3                                     __________________________________________________________________________    PREEMERGENCE HERBICIDAL ACTIVITY (% CONTROL)                                  Cmp                                                                           No SOY                                                                              WHT                                                                              CRN                                                                              ABUTH                                                                              IPOSS                                                                             STEME                                                                             XANPE                                                                             ALOMY                                                                              SETVI                                                                             SORHA                                   __________________________________________________________________________    1  100                                                                              80 95 100  100 100 95  80   100 95                                      2  60 70 80 100  100 90  60  70   100 90                                      3  60 30 40 100  100 100 100 ND   100 75                                      16 100                                                                              70 90 100  100 100 100 ND   100 100                                     17 70 50 85 100  100 95  80  ND   80  100                                     18 70 20 20 100  100 100 60  ND   100 80                                      24 30 50 70 100  100 ND  95  10   100 65                                      31 100                                                                              70 90 100  100 100 ND  70   100 100                                     32 100                                                                              40 70 100  95  90  ND  75   100 95                                      33 60 20 80 100  70  90  ND  70   100 80                                      34 80 50 70 100  100 100 ND  60   100 100                                     35 30 20 10 100  90  100 ND  30   100 50                                      36 70 30 30 100  100 60  ND  50   100 70                                      __________________________________________________________________________

                                      TABLE 4                                     __________________________________________________________________________    POSTEMERGENCE HERBICIDAL ACTIVITY (% CONTROL)                                 Cmp                                                                           No SOY                                                                              WHT                                                                              CRN                                                                              ABUTH                                                                              IPOSS                                                                             STEME                                                                             XANPE                                                                             ALOMY                                                                              SETVI                                                                             SORHA                                   __________________________________________________________________________    1  100                                                                              90 100                                                                              100  100 100 100 80   100 100                                     2  80 60 80 100  100 70  55  70   80  80                                      3  95 40 70 100  100 100 100 ND   100 60                                      16 95 60 90 100  90  100 100 100  100 100                                     17 80 50 90 100  100 100 60  80   100 100                                     18 80 40 75 100  100 100 90  80   100 80                                      24 80 30 80 100  100 10  100 30   80  80                                      31 95 50 85 100  100 100 100 75   100 100                                     32 95 40 80 100  95  100 100 70   100 90                                      33 90 40 80 100  100 80  100 60   100 80                                      34 90 50 85 100  90  75  100 65   100 95                                      35 80 25 70 100  80  30  100 30   80  60                                      36 80 30 80 100  100 100 100 50   80  75                                      __________________________________________________________________________     Rate of Application is 0.3 Kg/Ha                                              SOY is soybean, WHT is wheat, CRN is corn, ABUTH is velvetleaf, IPOSS is      morningglory, STEMME is chickweed, XANPE is cocklebur, ALOMY is               blackgrass, SETVI is green foxtail, and SORHA is johnsongrass                 ND is no data                                                            

Herbicidal compositions are prepared by combining herbicidally effectiveamounts of the active compounds with adjuvants and carriers normallyemployed in the art for facilitating the dispersion of activeingredients for the particular utility desired, recognizing the factthat the formulation and mode of application of a toxicant may affectthe activity of the material in a given application. Thus, foragricultural use the present herbicidal compounds may be formulated asgranules of relatively large particle size, as water-soluble orwater-dispersible granules, as powdery dusts, as wettable powders, asemulsifiable concentrates, as solutions, or as any of several otherknown types of formulations, depending on the desired mode ofapplication. It is to be understood that the amounts specified in thisspecification are intended to be approximate only, as if the word"about" were placed in front of the amounts specified.

These herbicidal compositions may be applied either as water-dilutedsprays, or dusts, or granules to the areas in which suppression ofvegetation is desired. These formulations may contain as little as 0.1%,0.2% or 0.5% to as much as 95% or more by weight of active ingredient.

Dusts are free flowing admixtures of the active ingredient with finelydivided solids such as talc, natural clays, kieselguhr, flours such aswalnut shell and cottonseed flours, and other organic and inorganicsolids which act as dispersants and carriers for the toxicant; thesefinely divided solids have an average particle size of less than about50 microns. A typical dust formulation useful herein is one containing1.0 part or less of the herbicidal compound and 99.0 parts of talc.

Wettable powders, also useful formulations for both pre- andpost-emergence herbicides, are in the form of finely divided particleswhich disperse readily in water or other dispersant. The wettable powderis ultimately applied to the soil either as a dry dust or as an emulsionin water or other liquid. Typical carriers for wettable powders includeFuller's earth, kaolin clays, silicas, and other highly absorbent,readily wet inorganic diluents. Wettable powders normally are preparedto contain about 5-80% of active ingredient, depending on the absorbencyof the carrier, and usually also contain a small amount of a wetting,dispersing or emulsifying agent to facilitate dispersion. For example, auseful wettable powder formulation contains 80.0 parts of the herbicidalcompound, 17.9 parts of Palmetto clay, and 1.0 part of sodiumlignosulfonate and 0.3 part of sulfonated aliphatic polyester as wettingagents. Additional wetting agent and/or oil will frequently be added tothe tank mix for postemergence application to facilitate dispersion onthe foliage and absorption by the plant.

Other useful formulations for herbicidal applications are emulsifiableconcentrates (ECs) which are homogeneous liquid compositions dispersiblein water or other dispersant, and may consist entirely of the herbicidalcompound and a liquid or solid emulsifying agent, or may also contain aliquid carrier, such as xylene, heavy aromatic naphthas, isphorone, orother non-volatile organic solvents. For herbicidal application theseconcentrates are dispersed in water or other liquid carrier and normallyapplied as a spray to the area to be treated. The percentage by weightof the essential active ingredient may vary according to the manner inwhich the composition is to be applied, but in general comprises 0.5 to95% of active ingredient by weight of the herbicidal composition.

Flowable formulations are similar to ECs except that the activeingredient is suspended in a liquid carrier, generally water. Flowables,like ECs, may include a small amount of a surfactant, and will typicallycontain active ingredients in the range of 0.5 to 95%, frequently from10 to 50%, by weight of the composition. For application, flowables maybe diluted in water or other liquid vehicle, and are normally applied asa spray to the area to be treated.

Typical wetting, dispersing or emulsifying agents used in agriculturalformulations include, but are not limited to, the alkyl and alkylarylsulfonates and sulfates and their sodium salts; alkylaryl polyetheralcohols; sulfated higher alcohols; polyethylene oxides; sulfonatedanimal and vegetable oils; sulfonated petroleum oils; fatty acid estersof polyhydric alcohols and the ethylene oxide addition products of suchesters; and the addition product of longChain mercaptans and ethyleneoxide. Many other types of useful surface-active agents are available incommerce. Surface-active agents, when used, normally comprise 1 to 15%by weight of the composition.

Other useful formulations include suspensions of the active ingredientin a relatively non-volatile solvent such as water, corn oil, kerosene,propylene glycol, or other suitable solvents.

Still other useful formulations for herbicidal applications includesimple solutions of the active ingredient in a solvent in which it iscompletely soluble at the desired concentration, such as acetone,alkylated naphthalenes, xylene, or other organic solvents. Granularformulations, wherein the toxicant is carried on relative coarseparticles, are of particular utility for aerial distribution or forpenetration of cover crop canopy. Pressurized sprays, typically aerosolswherein the active ingredient is dispersed in finely divided form as aresult of vaporization of a low-boiling dispersant solvent carrier, suchas the Freon fluorinated hydrocarbons, may also be used. Water-solubleor water-dispersible granules are free-flowing, non-dusty, and readilywater-soluble or water-miscible. The soluble or dispersible granularformulations described in U.S. Pat. No. 3,920,442 are useful herein withthe present herbicidal compounds. In use by the farmer on the field, thegranular formulations, emulsifiable concentrates, flowable concentrates,solutions, etc., may be diluted with water to give a concentration ofactive ingredient in the range of say 0.1% or 0.2% to 1.5% or 2%.

The active herbicidal compounds of this invention may be formulatedand/or applied with insecticides, fungicides, nematicides, plant growthregulators, fertilizers, or other agricultural chemicals and may be usedas effective soil sterilants as well as selective herbicides inagriculture. In applying an active compound of this invention, whetherformulated alone or with other agricultural chemicals, an effectiveamount and concentration of the active compound is of course employed.The compounds may be applied as preemergent or postemergent herbicides,with postemergent application preferred. For field use, where there arelosses of herbicide, application rates may be in the range of 10 to 300grams per hectare and are preferably in the range of 30 to 125 g/ha. Thecompounds of this invention are also useful as cotton defoliation andpotato dessication agents. Such agents aid in the harvesting of thecotton and potato crops.

The active herbicidal compounds of the present invention may also beused in combination with other herbicides. Such herbicides include, forexample: N-(phosphonomethyl)glycine, isopropylamine salt ("glyphosate");aryloxyalkanoic acids such as (2,4-dichlorophenoxy)acetic acid("2,4-D"), (4-chloro-2-methylphenoxy)acetic acid ("MCPA"),(+/-)-2-(4chloro-2-methylphenoxy)propanoic acid ("MCPP"); ureas such asN,N-dimethyl-N'-[4-(1-methylethyl)phenyl]urea ("isoproturon");imidazolinones such as2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-3-pyridinecarboxylicacid ("imazapyr"), a reaction product comprising(+/-)-2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-4-methylbenzoicacid and(+/-)2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-5-methylbenzoicacid ("imazamethabenz"),(+/-)-2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-5-ethyl-3-pyridinecarboxylicacid ("imazethapyr"), and(+/-)-2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-3-quinolinecarboxylicacid ("imazaquin"); diphenyl ethers such as5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid("acifluorfen"), methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate("bifenox"), and5-[2-chloro-4-(trifluoromethyl)phenoxy]-N-(methylsulfonyl)-2-nitrobenzamide("fomasafen"); hydroxybenzonitriles such as4-hydroxy-3,5-diiodobenzonitrile ("ioxynil") and3,5-dibromo-4-hydroxybenzonitrile ("bromoxynil"); sulfonylureas such as2-[[[[(4chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoicacid ("chlorimuron"),2-chloro-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide(achlorsulfuron"),2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sufonyl]methyl]benzoicacid ("bensulfuron"),2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-amino]sulfonyl]-1-methy-1H-pyrazol-4-carboxylicacid ("pyrazosulfuron"),3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]-2-thiophenecarboxylicacid ("thifensulfuron"), and2-(2-chloroethoxy)-N[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide("triasulfuron"); 2-(4-aryloxyphenoxy)alkanoic acids such as(+/-)-2[4-[(6-chloro-2-benzoxazolyl)oxy]phenoxy]propanoic acid(fenoxaprop"),(+/-)-2-[4-[[5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid("fluazifop"), (+/-)-2-[4-(6chloro-2-quinoxalinyl)oxy]phenoxy]propanoicacid ("quizalofop"), and (+/-)-2-[(2,4-dichlorophenoxy)phenoxy]propanoicacid ("diclofop"); benzothiadiazinones such as3-(1-methylethyl)-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide("bentazone"); 2-chloroacetanilides such asN-(butoxymethyl)-2-chloro-2',6'-diethyacetanilide ("butachlor");arenecarboxylic acids such as 3,6-dichloro2-methoxybenzoic acid("dicamba"); and pyridyloxyacetic acids such as[(4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)oxy]acetic acid("fluroxypyr").

It is apparent that various modifications may be made in theformulations and application of the compounds of the present inventionwithout departing from the inventive concepts herein, as defined in theclaims.

We claim:
 1. A compound having the formula ##STR18## R is hydrogen, halogen, or alkyl; R¹ is hydrogen, cyano, or alkyl;R² is hydrogen, or alkyl; R³ is hydrogen, straight or branched chain alkyl carbonyl, alkoxycarbonyl, alkylaminocarbonyl, or cycloalkylaminocarbonyl; X is hydrogen or halogen; Y is halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, or nitro; R⁴ is hydrogen, amino, straight or branched chain alkyl, haloalkyl, cyanoalkyl, alkoxyalkyl, arylalkyl, alkoxycarbonylalkyl, arylalkyl, alkoxycarbonylalkyl, alkenyl, alkynyl, or a salt-forming ion; and R⁵ is halogen.
 2. A compound of claim 1 where Q is 1-substituted-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl.
 3. A compound of claim 1 where Q is 4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yl.
 4. A compound of claim 1 where Q is 4-halo-5-difluoromethoxy-1-methylpyrazol-3-yl.
 5. A compound of claim 1 where Q is 3,4,5,6-tetrahydrophthalimid-1-yl.
 6. A compound of claim 1 where Q is 1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazole-5-on-1-yl.
 7. A compound of claim 1 where Q is 3-chloro-4,5,6,7-tetrahydroindazol-2-yl.
 8. A compound of claim 1 where Q is 5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-A]pyridin-3(2H)-on-2-yl.
 9. A compound of claim 1 where Q is 5,6,7,8-tetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazineimin-1-yl.
 10. A compound of claim 1 where Q is 4-methyl-1,2,4-triazine-3,5-dion-3-yl.
 11. A compound of claim 1 where Y and R are chloro; R¹ and R² are hydrogen or methyl; R³ is hydrogen or alkylaminocarbonyl; and X is fluoro.
 12. A compound of claim 11 where Q is 1-substituted-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl; and R⁴ is methyl or amino.
 13. A compound of claim 12 where R³ is methylaminocarbonyl.
 14. A herbicidal composition comprising a herbicidally effective amount of a compound of claim 1, and a herbicidally compatible carrier therefor.
 15. A herbicidal composition comprising an herbicidally effective amount of a compound of claim 1 and an herbicidally effective amount of one or more herbicides selected from the group consisting of glyphosate, 2,4-D, (4-chloro-2-methylphenoxy)-acetic acid, (+/-)-2-(4-chloro-2-methylphenoxy)-propanoic acid, isoproturon, imazapyr, imazamethabenz, imazethapyr, imazaquin, acifluorfen, bifenox, fomasafen, ioxynil, bromoxynil, chlorimuron, chlorsulfuron, bensulfuron, pyrazosulfuron, thifensulfuron, triasulfuron, fenoxaprop, fluazifop, quizalofop, diclofop, bentazone, butachlor, dicamba, and fluroxypyr.
 16. A composition of claim 15, and a herbicidally compatible carrier therefor.
 17. A method of controlling undesired plant growth, comprising application to the locus where the undesired plants are growing or are expected to grow, a herbicidally effective amount of a composition of claim
 14. 18. A method of controlling undesired plant growth, comprising application to the locus where the undesired plants are growing or are expected to grow, a herbicidally effective amount of a composition of claim
 15. 